1-benzyl-4-methoxy-3-methyl-1,4,5,6-tetrahydropyridine | 162465-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-4-methoxy-3-methyl-1,4,5,6-tetrahydropyridine
• 英文别名: 1-benzyl-4-methoxy-5-methyl-3,4-dihydro-2H-pyridine
• CAS: 162465-70-5
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: LEDWRDNLTRHJCE-UHFFFAOYSA-N

物化性质

• 沸点：
  337.8±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-methoxy-3-methyl-1,4,5,6-tetrahydropyridine 在 盐酸 、 aluminum oxide 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 7,8a-dimethyl-3,4,4a,8a-tetrahydro-1H-isoquinoline-2,5-dicarboxylic acid 2-benzyl ester 5-ethyl ester
  参考文献：
  名称：

  From a Biogenetic Scenario to a Synthesis of the ABC Ring of Manzamine A

  摘要：

  On the basis of a biogenetic proposal for explaining the biogenesis of manzamine A, the cycloaddition of dihydropyridinium salt 26 with diene derivative 5 leads to adducts 27. These adducts, as well as their related and previously described analogues 9, are now shown to be precursors of diene derivatives such as 10, 13, and 28. Treatment of diene 32 with sodium azide resulted in a one-step formation of the tricyclic imino derivative 34. This key intermediate was further transformed into tricyclic derivative 40, which possesses the essential features of the ABC ring of manzamine A.

  DOI：

  10.1021/jo0162033
• 作为产物：
  描述：

  1-benzyl-5-methyl-1,2,3,6-tetrahydropyridine 在 间氯过氧苯甲酸 作用下， 生成 1-benzyl-4-methoxy-3-methyl-1,4,5,6-tetrahydropyridine
  参考文献：
  名称：

  获得某些功能化的偶氮辛衍生物

  摘要：

  据报道，由易于获得的3-烷基-4-甲氧基-1,3,4,5-四氢吡啶1合成官能化的1,6,7,8-四氢偶氮cine碱7和1,2,7,8-四氢偶氮cine碱9。。

  DOI：

  10.1016/s0040-4039(00)01008-x

文献信息

• 3-Alkyl 1,6-dihydropyridines from 3-alkyl 5,6-dihydro-pyridinium salts. Implications in the biosynthesis of some macrocyclic marine alkaloids
  作者：Laurent Gil、Alice Gateau-Olesker、Christian Marazano、Bhupesh C. Das

  DOI：10.1016/0040-4039(94)02339-d

  日期：1995.1

  Additions of salts 1 and dihydropyridines 2 in an intramolecular manner have been invoked in the biosynthesis of some macrocyclic alkaloids such as manzamines, sarain A and halicyclamine A, recently isolated from sponges. We report conditions for the deprotonation of easily accessible salts 1, giving a regioselective entry to 3-alkyl 1,6-dihydropyridines 2. Also, we show that species 1 and 2 can be

  分子内添加盐1和二氢吡啶2已被用于生物合成一些最近从海绵中分离出来的大环生物碱，例如马扎明胺，sa仁A和盐环胺A。我们报告了容易获得的盐1的去质子化的条件，使区域选择性进入3-烷基1,6-二氢吡啶2。此外，我们表明，物种1和2可以从常见的中间体（例如9）中产生。二氢吡啶2在高温下不稳定，产生1,2-和1,4-二氢吡啶异构体，但很容易被亲二烯体捕获，以合成有用的异喹核苷，例如18或20。
• An access to some functionalized azocine derivatives
  作者：Laurent Gil、Rossimiriam Pereira de Freitas Gil、Daniela Cristina dos Santos、Christian Marazano

  DOI：10.1016/s0040-4039(00)01008-x

  日期：2000.8

  The syntheses, from readily accessible 3-alkyl-4-methoxy-1,3,4,5-tetrahydropyridine 1, of functionalized 1,6,7,8-tetrahydroazocine 7 and 1,2,7,8-tetrahydroazocine 9 are reported.

  据报道，由易于获得的3-烷基-4-甲氧基-1,3,4,5-四氢吡啶1合成官能化的1,6,7,8-四氢偶氮cine碱7和1,2,7,8-四氢偶氮cine碱9。。
• From a Biogenetic Scenario to a Synthesis of the ABC Ring of Manzamine A
  作者：Matthias Herdemann、Ali Al-Mourabit、Marie-Thérèse Martin、Christian Marazano

  DOI：10.1021/jo0162033

  日期：2002.3.1

  On the basis of a biogenetic proposal for explaining the biogenesis of manzamine A, the cycloaddition of dihydropyridinium salt 26 with diene derivative 5 leads to adducts 27. These adducts, as well as their related and previously described analogues 9, are now shown to be precursors of diene derivatives such as 10, 13, and 28. Treatment of diene 32 with sodium azide resulted in a one-step formation of the tricyclic imino derivative 34. This key intermediate was further transformed into tricyclic derivative 40, which possesses the essential features of the ABC ring of manzamine A.
• Synthesis of New Azocine Derivatives and Their Functionalization by Nucleophilic Addition to Their Iminium Salts
  作者：Angela Cristina Leal Badaró Trindade、Daniela Cristina dos Santos、Laurent Gil、Christian Marazano、Rossimiriam Pereira de Freitas Gil

  DOI：10.1002/ejoc.200400728

  日期：2005.3

  eight-membered nitrogen heterocycles 20a,b is described starting from the 3-alkyl-N-benzylpyridinium salts 14a,b. These azocine derivatives were converted into their respective iminium salts 11 by treatment with methanesulfonic acid. A study concerning the regioselectivity of nucleophilic additions to these salts is presented. Nucleophiles like hydride or Grignard reagents react selectively in the 2-position

  描述了从 3-烷基-N-苄基吡啶鎓盐 14a、b 开始生成八元氮杂环 20a、b 的路线。通过用甲磺酸处理，这些偶氮辛衍生物被转化为它们各自的亚胺盐11。介绍了对这些盐的亲核加成的区域选择性的研究。亲核试剂如氢化物或格氏试剂在 2 位选择性反应生成加合物，如 22 和 23，而叠氮化物和苯硫醇盐分别攻击 6 位生成 24 和 25。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)